Shawn Michaels defeats Bret Hart

WrestleMania XII

After the two legends beat the hell out of each other for 60 minutes, Gorilla Monsoon ordered the fight into overtime to break the draw. Two minutes in, the Heartbreak Kid pinned Hart and the boyhood dream finally came true for Michaels. Michaels outlasted Hart and proved that he was not just a boy toy anymore -- he became the WWF Champion.